Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? — only cruises that fit entirely inside your dates
My result then click any cruise row to open it
Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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+ pick specific cruise lines · 2 selected
Luxury Azamara Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering Cunard ×Azamara ×Visits Dominica × Clear all
Showing 20 of 20 sailings
Azamara · Azamara JourneyRound-trip
Caribbean 14 nights Nov 14 – Nov 28, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados15 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +8 more
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from $4,856
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Azamara · Azamara JourneyOne-way
Caribbean 6 nights Dec 12 – Dec 18, 2026 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico7 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +3 more
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from $1,645
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Cunard · Queen Mary 2Repositioning
Northern Europe 21 nights Dec 12 – Jan 2, 2027 from Southampton, England to New York, New York
Southampton, England · New York, New York · … · New York, New York9 ports
Southampton, England · New York, New York · Road Town, Tortola, B.V.I. · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · Dominica, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · New York, New York
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourNorman IslandRandom Wind 'Paradise Day Sail' +4 more
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from $3,310
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Cunard · Queen Mary 2Repositioning
Northern Europe 23 nights Dec 19 – Jan 11, 2027 from New York, New York to Southampton, England
New York, New York · Road Town, Tortola, B.V.I. · … · Southampton, England9 ports
New York, New York · Road Town, Tortola, B.V.I. · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · Dominica, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · New York, New York · Southampton, England
★ Bucket-list Manhattan Helicopter TourNorman IslandRandom Wind 'Paradise Day Sail'Swim with wild green sea turtles + two shipwrecks… +4 more
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from $3,389
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Cunard · Queen Mary 2Round-trip
Mediterranean 34 nights Jan 11 – Feb 14, 2027 from Southampton, England
Southampton, England · Funchal, Madeira, Portugal · … · Southampton, England12 ports
Southampton, England · Funchal, Madeira, Portugal · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · St. Lucia, Caribbean · Grenada, Caribbean · Dominica, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Amber Cove, Dominican Republic · Philipsburg, St. Maarten · Santa Cruz de Tenerife, Canary Islands · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Pico do Arieiro to Pico RuivoNorman IslandSwim with wild green sea turtles + two shipwrecks… +6 more
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from $7,369
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Azamara · Azamara QuestRound-trip
Caribbean 15 nights Nov 6 – Nov 21, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico16 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay Beach +9 more
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from $5,751
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Cunard · Queen Mary 2Round-trip
Northern Europe 27 nights Nov 12 – Dec 9, 2027 from Southampton, England
Southampton, England · New York, New York · … · Southampton, England10 ports
Southampton, England · New York, New York · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater Hike +4 more
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from $3,489
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Azamara · Azamara QuestRound-trip
Caribbean 14 nights Nov 14 – Nov 28, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados15 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +8 more
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from $5,331
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Cunard · Queen Mary 2Round-trip
Caribbean 13 nights Nov 19 – Dec 2, 2027 from New York, New York
New York, New York · St. Thomas, U.S. Virgin Islands · … · New York, New York8 ports
New York, New York · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +3 more
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from $1,899
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Azamara · Azamara QuestRound-trip
Caribbean 14 nights Nov 21 – Dec 5, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · San Juan, Puerto Rico15 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +8 more
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from $5,341
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Azamara · Azamara QuestOne-way
Caribbean 7 nights Nov 28 – Dec 5, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +4 more
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from $2,449
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Azamara · Azamara QuestRound-trip
Caribbean 14 nights Dec 5 – Dec 19, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · San Juan, Puerto Rico15 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +8 more
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from $5,021
Book This Cruise@ Cruisebound
Azamara · Azamara QuestOne-way
Caribbean 7 nights Dec 12 – Dec 19, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +4 more
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from $2,383
Book This Cruise@ Cruisebound
Cunard · Queen Mary 2Repositioning
Northern Europe 20 nights Dec 14 – Jan 3, 2028 from Southampton, England to New York, New York
Southampton, England · New York, New York · … · New York, New York8 ports
Southampton, England · New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +3 more
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from $3,053
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Cunard · Queen Mary 2Repositioning
Northern Europe 21 nights Dec 21 – Jan 11, 2028 from New York, New York to Southampton, England
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Southampton, England8 ports
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeGros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $3,086
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Azamara · Azamara QuestOne-way
Bahamas 9 nights Dec 27 – Jan 5, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Kralendijk, Bonaire, Dutch Antilles · … · Miami, Florida7 ports
Bridgetown, Barbados · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Puerto Plata, Dominican Republic · Nassau, Bahamas · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Klein BonairePrivate Full-Day Curaçao Island Tour with Local Ex…Aruba +3 more
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from $3,591
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Cunard · Queen Mary 2Round-trip
Mediterranean 35 nights Jan 11 – Feb 15, 2028 from Southampton, England
Southampton, England · Santa Cruz de Tenerife, Canary Islands · … · Southampton, England13 ports
Southampton, England · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Grenada, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Funchal, Madeira, Portugal · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Teide National ParkRandom Wind 'Paradise Day Sail'Gros Piton Summit Hike +7 more
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from $4,899
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Cunard · Queen Mary 2Round-trip
Northern Europe 28 nights Feb 27 – Mar 26, 2028 from Southampton, England
Southampton, England · New York, New York · … · Southampton, England9 ports
Southampton, England · New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +3 more
View →
from $4,859
Book This Cruise@ Cruisebound
Cunard · Queen Mary 2Repositioning
Caribbean 20 nights Mar 6 – Mar 26, 2028 from New York, New York to Southampton, England
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Southampton, England8 ports
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeGros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $15,039
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Azamara · Azamara QuestOne-way
Caribbean 9 nights Mar 13 – Mar 22, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Miami, Florida8 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Castries, St. Lucia · Saint- Pierre · Roseau, Dominica · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourCosol ToursBoiling Lake Hike +3 more
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from $3,932
Book This Cruise@ Cruisebound

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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara